Parky - I have layers and I too find a high ponytail painful under a cycle helmet. I tend to have the upper half of my hair in one ponytail, then for the swim, I put it all in a high ponytail but not pulling it all through (to create a bun effect). After the swim I put it in a low ponytail so it comes below the helmet. Depending on how I feel I may leave it like that or put it back in a high ponytail for the run. All throughout the Tri, I keep the upper half pulled off my face.